Allyl bromide → HCID 14718697, compound

HRID 1088299Notes

Reaction equation

HRID 1088299 reaction equation
[CH3:1][C:2]([CH3:10])([CH3:9])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH2:11](Br)[CH:12]=[CH2:13]>O1CCCC1>[CH3:1][C:2]([CH:3]([CH2:13][CH:12]=[CH2:11])[C:4]([O:6][CH2:7][CH3:8])=[O:5])([CH3:10])[CH3:9]

Participants

4

Reactant 2

HCID 7841Allyl bromideHCID 79284Ethyl 3,3-dimethylbutyrate

Product 1

HCID 14718697HCID 14718697, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

The reaction mixture was then allowed to warm to 0° C. before being cooled to -70° C. A solution of ethyl 3,3-dimethylbutanoate (14.4 g) in dry tetrahydrofuran (20 cm3) was then added dropwise to the reaction mixture which was maintained at -70° C. After the addition was complete, the reaction temperature was allowed to rise to -60° C. for 15 minutes, before being cooled again to -70° C. A solution of allyl bromide (13.4 g) in dry tetrahydrofuran (5 cm3) was then added in portions to the reaction mixture, which was allowed to warm to the ambient temperature, and stirred for a further 16 hours.

Workup

  1. temperaturebefore being cooled to -70° C
  2. temperaturewas maintained at -70° C
  3. additionAfter the addition
  4. temperaturebefore being cooled again to -70° C
  5. temperatureto warm to the ambient temperature

Sources & evidence

ORD record
ord-fb51c5f7226542a8812753d92a8f9d22
Source dataset
uspto-grants-1990_10
Patent number
US04962109

Reaction notes

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